Like natural glycan-binding proteins, these receptors bind pyranosides by accessing multivalent and cooperative interactions, and these studies suggest a new approach towards biomimetic synthetic carbohydrate receptors, where conformational flexibility and promiscuity are incorporated into design. The first-principles modelling suggests that 10⋅β-Man forms an inclusion-type complex where the glycan engages both monomeric subunits of 10 through H-bonding and C−H⋅⋅⋅π interactions. A variety of 1D and 2D NMR, and computational techniques were used to determine the thermodynamic binding parameters (Δ H o and Δ S o) and the structure of the host–guest complex, revealing that dimeric receptor 10 binds β-Man with increased enthalpy, but a larger entropic penalty than 1. Although the receptors are promiscuous, 1 shows selectivity for β-Man at a ratio of 103:1 β-Man:β-Gal, receptors 2– 4 and 6 have preference for α-Man, 5 is selective for β-Gal, and 10 prefers α-Glc (Man=mannose Gal=galactose, Glc=glucose). /0000-0001-7035-1525 Hunter College and the Graduate Center, CUNY. Herein the binding of 8 receptors with 5 distinct octyloxy pyranosides, which was measured by mass spectrometry and by 1H NMR titrations in CD 2Cl 2 at 298 K, is reported, providing binding affinities that vary from ≈10 1–10 4 m −1.
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